The Biggest Sports Bets Made By Celebrities

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Photo by Sergey Zolkin

Many celebrities endeavour to keep their lives private, but thanks to social media in particular, details can leak out. Sometimes it’s hard to contain excitement over things like winning a sports bet.

Nowadays sports betting is not a hobby of the elite and is legal in many parts of the world. To find a reliable bookmaker, you have to check the list of the best betting sites in your country. For instance, if you live in Romania, you can look through the one published at, and if you live in the UK or Nigeria, you can find similar ratings based on important parameters.

But celebrities with bigger bank balances than most of us could ever imagine also enjoy a wager. As the examples listed below of some of the biggest sports bets made by celebrities illustrate, often more is staked in one wager than most people make in a lifetime.

But that is what makes this all so intriguing. While the odds on the single outcome of a sporting event are the same for anyone, when 100k or more is being dropped on a bet, then things get far more interesting.

Floyd Mayweather, Jr. Doesn’t Pull Punches

Rumours persist that former pro boxer Floyd Mayweather lost around $13M on the outcome of the 2014 Super Bowl. He allegedly bet more than $10M on a pre-match selection for the Denver Broncos to beat the Seattle Seahawks and a smaller $2.6M for the Broncos to be leading at halftime.

Mayweather has never confirmed that he placed the wagers, but if he did, he would have been down $13M as the Broncos lost 43-8. Mayweather has gone public on his socials before with winning bets, including a $1M success on the Oregon Ducks in 2012.

‘Winning’ Charlie Sheen

While some celebrities like Sebastian Stan are more well-known for philanthropic work, others like Charlie Sheen have been more known for excess. Famous for ‘winning’, actor Charlie Sheen backed a dream he had about the outcome of a 2008 boxing match between Manny Pacquiao and Oscar De La Hoya.

Sheen had dreamt that Pacquiao was going to dominate, which he did, and reportedly collected $1M from the forecast. Sheen then said he was going to give up betting because the huge success didn’t do anything for him.

50 Cent NFL

One of the most famous celebrity sports bets of all time came from rapper 50 Cent in 2012. He landed an NFL success by forecasting that the pre-match favourites the New England Patriots would fall to his hometown New York Giants at Super Bowl XLVI.

That’s exactly what happened, with the Giants winning 21-17. That’s not the first example of 50 Cent, real name Curtis Jackson, winning big on the NFL. He also successfully bet $500K on the Giants to win the 2011 NFC Championship game.

Is The ‘Drake Curse’ Real?

Drake is one of the most prominent celebrities when it comes to sports betting. He has, however, gained a reputation for not being the most successful bettor. The ‘Drake Curse’ has seen him lose some big bets.

He lost more than $1.5 million on Alex Pereira to beat Adesanya in a UFC bout, plus around $3 million on Jake Paul to beat Tommy Fury in boxing. Drake failed in backing France to win the 2018 World Cup Final (90 minutes).

But his successes do include big returns from the 2023 Super Bowl and a huge NFL parlay win worth almost $2 million.

Ashton Kutcher Plays It Dumb

Actor Ashton Kutcher took a different approach to his betting. He revealed in an interview that he was once part of a gambling syndicate, happy to use his ‘dumb actor’ persona from his role in That 70s Show to take on the bookmakers.

Kutcher revealed that he placed American Football bets for half a season and cleared three-quarters of a million in US dollars in doing so. He went on to invest in an esports betting startup with Shark Tank’s Mark Cuban in 2015.

The List

Many other celebrities have gambled not only on sports but on casino games like blackjack and poker including Phil Mickelson, Charles Barkley, Michael Jordan and Leonardo di Caprio.

There’s a famous story about Ben Affleck giving away all of his winnings from a night of blackjack with Matt Damon in Las Vegas to casino staff. UFC boss Dana White reportedly won $2M in just three months at blackjack in Las Vegas while Poker champion Phil Ivey once lost a huge chunk on the wrong pick at Super Bowl XLIV.